Method for synthesizing compound and catalyst for synthesis reaction

Abstract

To provide a catalyst for synthesis reaction which can achieve good yield in the Sonogashira reaction and also can be recovered after the reaction, and a method for synthesizing a compound in which the catalyst for synthesis reaction is used, a perovskite-type composite oxide containing palladium is used as the catalyst for synthesis reaction in the Sonogashira reaction represented by the following reaction scheme (1): R 1 —X+HC≡CR 2 →R 1 C≡CR 2   (1)

1. A method for synthesizing a compound, comprising:
 reacting a compound represented by the following formula (1) with a compound represented by the following general formula (2) in a presence of a perovskite-type composite oxide containing palladium:
   R 1 —X  (1) 
 
 wherein R 1  represents an aryl group which may have a substituent, a heterocyclic group which may have a substituent or an alkenyl group which may have a substituent, and X represents a halogen atom excluding fluorine, a trifluoromethanesulfonyloxy group, and
   HC≡CR 2   (2) 
 
 wherein R 2  represents a hydrogen atom, an aryl group which may have a substituent, a heterocyclic group which may have a substituent, and alkyl group which may have a substituent, an alkenyl group which may have a substituent or trialkyl-substituted silyl group. 
 
     
     
       2. The method for synthesizing a compound according to  claim 1 , wherein the perovskite-type composite oxide containing palladium is represented by the following formula (3):
   AB 1−z Pd z O 3   (3) 
 wherein A represents at least one element selected from rare-earth elements and alkaline earth metals, B represents at least one element selected from transition elements excluding rare-earth elements and Pd, and A1, and z represents an atomic ratio of Pd. 
 
     
     
       3. The method for synthesizing a compound according to  claim 1 , wherein the perovskite-type composite oxide containing palladium is represented by the following formula (4):
   A 1−x A′ x B 1−(y+z) Cu y Pd z O 3   (4) 
 wherein A represents at least one element selected from rare-earth elements, A′ represents at least one element selected from alkaline earth metals, B represents at least one element selected from transition elements excluding rare-earth elements, Cu and Pd, and A1, x represents an atomic ratio satisfying the following relation: 0≦x≦0.5, y represents an atomic ratio satisfying the following relation: 0<y≦0.5, and z represents an atomic ratio satisfying the following relation: 0<z≦0.5. 
 
     
     
       4. The method for synthesizing a compound according to  claim 1 , wherein the perovskite-type composite oxide containing palladium is represented by the following formula (5):
   AB 1−(y+z) Cu y Pd z O 3   (5) 
 wherein A represents at least one element selected from Y, La, Ce, Pr and Nd, B represents at least one element selected from Mn, Fe, Co and Al, y represents an atomic ratio satisfying the following relation: 0<y≦0.5, and z represents an atomic ratio satisfying the following relation: 0<z≦0.5.